


Peculiar encounter- How Rose lost her virginity to a future version of her brother with the help of a future version of herself

by Raptarion



Category: Homestuck
Genre: Age Difference, Creampie, F/F, F/M, Incest, Loss of Virginity, Mildly Dubious Consent, Multi, Self-cest, Sibling Incest, Size Difference
Language: English
Status: Completed
Published: 2015-01-14
Updated: 2015-01-14
Packaged: 2018-03-07 11:04:15
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 5,012
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3172148
Author URL: https://archiveofourown.org/users/Raptarion/pseuds/Raptarion
Summary: <blockquote class="userstuff">
              <p>I think the title explains it all.</p>
            </blockquote>





	Peculiar encounter- How Rose lost her virginity to a future version of her brother with the help of a future version of herself

Originally, her goal was to map out the meteor. She figured it would be a nice diversion from other activities. A way to kill time when she needed a break from the shenanigans of the rest of the group. She had not anticipated the inner structure of the hunk of rock to be so complex. Nor had she accounted for how nearly ever hallway looked the same. She probably should have anticipated the Gamzee would make things more difficult by constantly moving otherwise invaluable landmarks. Chests and test tubes that were there one day had either been moved to another part of the room, or removed entirely. The same went with chalk drawing. She soon gave up on her endeavor to chart the many corridors furthest away from their designated living area. But she did not consider these trips any less invaluable to her desire for private time. She would often venture out into the dimly lit unknown, passing by rooms both familiar and unfamiliar. She saw many oddities in her explorations. But not in her wildest dreams did she expect to find what she was about to stumble across.

She was no stranger to odd lights in her travels. The meteor had an abundance of machinery. Most of it still somewhat operational, and giving off a faint glow. So when she saw, through a maze of pipes and wires, a glowing light, she was not surprised. As she got closer, she did find it curious that the light was warmer than she was used to from the seemingly perpetual green hue of the computer screens. She found it curious how much brighter the light was than she was used to. And she found it curious how there were shadows moving in the light. Figures moving about in the space ahead of her. Then the figures spoke, and the voices that reached her ear she found the most curious.

"Not that spending time in this dump again isn't great and all, but we've been here for almost an hour." Came a voice, indisputably masculine, and almost familiar. It sounded almost like-  
"Dave, you're hurting my feelings. Here I was thinking I've been a marvelous conversation partner. Yet you tire of me in less than an hour?" A soft mysterious voice, that Rose recognizes as her own. Although undoubtedly more mature.  
"You couldn't have gotten the timing a bit better?" The Dave who's voice didn't crack asked.  
"I wanted time to set up the room. And you should know better than anyone how difficult it is to pinpoint exact times and places on a moving object out here. Really though I'm starting to suspect this is more than boredom provoking these question. Could it be you're impatient for our guest to arrive? Are you squirming under the weight of your anticipation?" The Rose who sounded more woman than girl asked. She made the word anticipation sound dirty.  
"Are you trying to get under my skin with those mind games again? Those don't work on me anymore." Almost certainly future Dave says.  
"I did think it strange how easy it was to convince you to go along with this." Future Rose continues as if Dave hadn't said anything. "I wonder if this is just a general lust for impressionable young girls, or just an unrequited desire for me in particular. A need to feel like you have power and control over a childhood opponent who was the object of many sexually confused thoughts, charged with the turbulent cocktail of hormones one experiences with the onset of puberty?"

There's silence. She can't tell if that actually got under Dave's skin or not. She stands there, in the obscuring jumble of pipes and wires, wondering if she should go on. It seemed like they were waiting for her, if she was reading Rose's playful accusations of Dave's perversions correctly. But she was reluctant to meet future versions of herself or her friends. Time shenanigans like this never seemed to be anything but trouble.  
Eventually she sighs to herself quietly and continues her way towards the light. Not going to meet with them would only hurt matters by upsetting stable time loops after all.

She squeezes her way past a few more pipes to a room of sorts. One with only one wall, and a massive maze of pipes and machinery in every direction. The cold metal of the floor was covered up with a large rug. The source of the light was revealed to be number of lamps on end tables. There was a number of armchairs and love seats, surrounding a coffee table in the center of the rug. The room could easily seat a dozen people. An alchemiter in the corner reveals the likely origin of this furniture, which had no real other way of getting here through the cramped cluster of pipes.

And there was Dave and herself, lounging on a love seat and arm chair respectively. Both significantly older. Mid to late twenties if she had to guess. She was dressed in a purple skirt, and a black shirt, decorated with a picture of a dark green octopus with vicious angry eyes. The tentacles of the octopus were draped over a pile of skulls, tendrils weaving in and out of eye sockets. Dave had on a much more simple white tank top with khaki cargo shorts. What caught her eye wasn't their clothes though. No, it was their figures. It was strange seeing her and Dave grown up. She had filled out nicely, getting some eye catching curves along the way. And Dave. Somewhere between now and whatever time they came from, Dave got ripped. He was rather handsome now too. Rose feels heat rise to her face as she realizes she is ogling her future self and brother. She swallows to clear her throat, and tries to regain her composure.

"Hello. To what do I owe the pleasure?" She asks. The two look up, only just now noticing her.  
"Au contraire." Her future self says with a sly smile. "The pleasure is all ours."  
"Yo." Dave says, waving nonchalantly from his position on the love seat, stretched out with his feet on one of the arm rests. In contrast, Rose sat with her legs crossed, and her hands folded neatly in her lap.  
"Feel free to take a seat. I could alchemize something to eat if you'd like."  
"We getting some food? I could go for a pizza." Dave says.  
"I'm fine." Rose says, taking a seat. Her future self goes to the alchemiter and in a few moments came back with a plate of grilled chicken and green olive pizza. Dave takes a slice and begins eating. It occurs to Rose that her future self hadn't asked what kind of pizza Dave wanted, meaning she knew off hand what toppings he liked.

"So. I assume you're here to give me some advice? Or tell me something important?" Rose asks.  
"No." Her future self replies.  
"...no?" She wasn't expecting that.  
"We're just here to visit." Future Rose says, sauntering up to the chair her younger self was sitting on.  
"That seems like a reckless misuse of time travel." Rose says, watching as her older self trails around to the back of the chair.  
"See. That's what I said." Dave chips in.  
"But you changed your tune what I said what the trip was all about." Rose's older self said. Rose feels the arms of her older double drape over her shoulders to cross lazily across her chest. Rose shudders a bit at the unexpected contact.  
"And what are you here for?" Rose asks. Dave averts his gaze. You swear he's blushing. What the hell is going on here?  
"You see. Many years ago, in this room. I stumbled across an older version of myself and Dave. And during this encounter..." The older Rose says, before leaning in close and changing her voice to a whisper. "I lost my virginity."  
Rose could feel her entire body stiffen, heat rising to her face and causing her to blush right down to her navel. Had she heard that right? Was her older self messing with her? Was this all some elaborate joke she had devised to poke fun at herself as a gullible child? She didn't have time to contemplate these possibilities in depth because her older self was still whispering right in her ear.  
"An older Rose fondled me. Stripped me bare and presented me like a gift to an older version of Dave. I can still remember how effortlessly he lifted me up, and how big he was." As she talks, she roams her hands over her abdomen and sides. Slowly getting lower.  
"Rosie. Not feeling all that comfortable over here with you whispering conspiracies over there." Dave says.  
"No need to be so suspicious brother mine." Rosie says. Dave cringes a bit at that.  
Did he just call her Rosie? And brother mine? Did they have pet names?  
"I... uh." Rose starts to say something. But even though the words seemed so clear in her head, when she tries to say them they disappear completely. What was this? Was this actually happening?  
"Oh my. I am flustered aren't I?" Rosie asks rhetorically. "Don't you want to come join in on the fun Dave? This might be the only chance you get to be more on top of the situation than I am... or at least, more on top than one of me."  
"I think I'm gonna sit back for a bit longer."  
"And after you seemed so eager when I told you we were going back to fuck my younger self." Rosie says brazenly.  
"That was- I just wanted- time loops-" Dave sputters out.  
Rose could practically feel her older self grinning as she casually fondles her chest and rubs her thigh. She was still coming to grips with all of this. This was really happening. She just walked into some bizarre incestuous three-way and was getting felt up by herself from the future.

"I think you could do without these." Rosie says, picking at her god tier robes. "They're just going to get in the way."  
Rose considers some objections. She even briefly considers voicing them. But she had a feeling they would fall on deaf ears. Rosie makes her way around the front of the chair, and she gets a good look at her face. A lustful and predatory grin painted her features. She was enjoying this a lot. She slips her hands up her legs and grips hold of the waistline of her pants. She slides them off, forcing Rose to wiggle awkwardly to let her do so. She suddenly remembers what kind of underwear she has on and blushes even more intensely. They were embarrassingly childish. If she had known that she was going to be having sex this evening, she wouldn't have gone for a pair decorated with colorful squiddles.  
Rosie then goes to pull off her panties. Rose shifts again to allow the removal of the embarrassing garment. With the way she had been lording over her and her embarrassment, as well as teasing Dave about the situation, she was sure to get a kick out of showing off her childish underwear.  
It was therefore with no small amount of relief that she tucked the offending pair of panties into her god tier pant-leg, keeping it out of sight of Dave. She smiles up at Rose, a smile much kinder than earlier. She stands up and leans over to whisper in her ear again.  
"I know you're feeling nervous. I was in your shoes after all. But relax. We both know I wouldn't do this if I wasn't sure you'd like it."  
"I am nervous." Rose says, finally finding her voice again. "This is all really sudden. And I don't feel too comfortable with the situation... especially just being stripped like this." She pulls on the hem of her shirt, squeezing her legs together to help cover her lower naked half as best she could.  
"I think I have something that will help you feel a bit more at ease."

"Dave. It's not fair if young Rose is the only one getting undressed here. Care to start showing a bit more skin yourself?" She asks.  
Dave looks over at the two different versions of his sister.  
"Uh. Sure." He says, standing up. He unbuttons his shorts and lets them fall to the ground, revealing a pair of white and red stripped boxers. He steps out of them as he grabs the hem of his tank-top and pulls it over his head. Rose gulps at the sight of Dave's bare chest and stomach. He had to be flexing right? There's no way his torso was that perfectly muscular without him making a conscious effort.  
"Would you like me to undress too?" Rosie asks.  
"Don't you already know the answer?" Rose asks in return.  
"I think it's only polite to ask." She responds.  
"You can undress at your leisure I guess." Rose says, wanting to see more of her body, but not entirely sure she liked the idea of comparing the body of her sexy older self to her still undeveloped teen body. The fact that her older self probably knew that she was thinking this made her feel embarrassed all over again, it suddenly occurring to her how she had no privacy, even in her thoughts. As if sensing this insecurity, Rosie gives her a reassuring smile. Rose felt a little better at the gesture. Then she reaches out to grab the him of her shirt. She pulls up, and Rose lifts her arms somewhat hesitantly to allow her to remove her shirt. All that was left was her training bra. Plain white, and not nearly as embarrassing as her panties. Rosie casually reaches around her back to unhook the bra. She pulls it away, and like that, she was completely naked.  
"Care to move over to one of the larger seats? It would be more comfortable." Rosie asks.  
"Sure." Rose replies, very conscious of her nakedness. Rosie leads the way to the loveseat Dave was previously occupying, and Rose follows. She passes near Dave on the way, and notices a distinctive bulge in his boxers. She looks up at him, and catches his eyes behind his sunglasses. He was looking right at her. He quickly looks away. Rose inexplicably feels better as a result of this. Dave found her sexy, which made her feel more confident standing next to the bombshell of her older self. And the way he felt embarrassed about his attraction made her feel like she wasn't alone in her complete lack of control in this situation. Dave was just as confused about all this as she way. Probably more so in fact.

She goes to sit down in the chair, but Rosie's hands grab onto her hips and redirect her to sit in her lap. She feels her hot breath on her neck. Her hand rubs up her thighs again, coming to cup her pussy. Her fingers rub around her entrance, spreading her juices around. She hadn't realized it before, between all of the embarrassment and tension. But she had gotten incredibly wet. Some part of her was clearly getting off on all this. As Rosie rubs her fingers up and down her lower lips, she also trails her fingers over her chest, cupping her near nonexistent breasts, and flicking her fingers lightly over her nipples. She had never found herself particularly sensitive there. But something about Rosie doing it was doing it for her. Maybe it's because she was more experienced teasing her breasts? Or because someone else was doing it?  
"Dave. Get out of those boxers already. I think you've been hiding the goods long enough." Rosie commands. Dave doesn't comment. He just slips his underwear down his legs and... and...  
"Holy shit." Rose says. There was no way she actually intended that to go inside her right? It looked huge! And it wasn't even at full mast yet. She wasn't exactly intimately familiar with male sex organs. But even she could tell it was still only half hard.  
"Get over here brother mine." Rosie says. Dave grimaces again. But his cock also twitches, and seems to get a bit harder at her words. It seemed he balanced a great deal of guilt and arousal when it came to fucking his sister. He walks over to the love seat, and Rosie reaches out to pull him closer by his dick. Rose looks up as her older self begins slowly moving her hand up and down his phallus. She watches with interest and fear as Dave is jacked off by Rosie.

Suddenly she feels herself being penetrated by Rosie's fingers. She clenches down in shock at first before relaxing under the steady rhythm of her fingers working in and out of her. Rose considers the skill with which her older self manages to handle pleasuring two partners at once. Did she have a lot of practice? She thinks it best not to ask. Now probably wasn't the best time. She goes back to watching Rosie work, looking up to see her reach out with her tongue to lick the head of his shaft, then bring it into her mouth. She checks Dave's expression every once in a while, finding herself enjoying the normally composed Strider struggle to keep a straight face while his sister goes down on him. The expressions he made were priceless, and strangely arousing. He furled his brow. Clenched his teeth. There's even a point where he bites his lip, but she cant see exactly what Rosie did to get that reaction.

"I think you're both ready." Rosie says, shifting Rose off her lap to lay down in the love seat. Rose watches as her older double stands up and pulls out a bottle of something. She squeezes a clear gel onto her fingers and begins spreading it inside and around her cooch. Rose shivers a bit at the sensation. It was kind of cold.  
"Lubricant. You're wet enough already, but you can never have too much. Especially in situations like this."  
Rose assumes that she is referring to situations where your well hung brother is going to plow the tight virgin depths of his underage sister. She feels the nerves from earlier returning as Rosie spreads the lube over Dave's intimidating dick. She reminds herself that her older self had assured her she would like it. But seeing how much she was going to need to stretch to allow him inside was enough to make her wonder just how well she remembered this night.

"You ready?" Dave asks, aligning his large muscular body over her. One arm next to her head to keep himself upright, and the other lining the tip of his dick up to the entrance of her pussy.  
"Good question. I have no idea." Rose says in response, looking up at his face, as uncertain as she felt.  
"You'll be fine. Just make sure to go really slow Dave." Rosie says. As she speaks, she reaches down to unbutton her skirt, taking it off and tossing it to the side carelessly. Rose sees that she is wearing black lacy panties. Very sexy underwear that barely left anything to the imagination. Her attention is pulled away from watching herself undress by the tip of Dave's cock rubbing up and down near her entrance. She shudders in anticipation and apprehension. Then, slowly, he pushes into her.

Her entrance is unyielding. Refusing to grant Dave entry. It was as sure as she was that he was too big. Dave pulls back for a moment, before going in again. He once again finds his way forward stubbornly blocked by a too small opening. But he isn't giving up that easily. Time and again he pushes forward, and slowly she feels her entrance yield. She grits her teeth as she is slowly stretched by the head of Dave's cock. She grips the upholstery of the love seat tightly as he finally get the head all the way in. He pushes in a tiny bit before retreating a bit. Then pushes in, a mere centimeter deeper, before pulling back. Bit by bit he spreads open the inside of her pussy, giving his dick room to move. She watches his face as he slowly fucks her. It was a face of deep concentration, fighting the sensations of her inner walls squeezing him tightly, and trying his best to slowly accommodate her to his size. She wraps her arm around his, holding on as he finally goes as deep as he can. She sighs out a feeling of contentedness. She could feel so much of him filling her up. If she focused, she could almost swear she felt his pulse through his member.

"Finally bottomed out huh?" Rosie asks. She looks over to see that, in the time it had taken for Dave to fill her completely, Rosie had stripped out of everything but her revealing panties.  
"This is as deep as I can go alright." Dave says.  
"Well that sounds like the signal to really start giving Rose the ride of her life. Why don't you switch positions a bit. I think she would like to feel just how strong you are.  
Rose wonders what her future self has in mind. Whatever it was, she had a feeling she would find out pretty quickly.  
"Come on Dave. Sit up." She commands. Dave slowly pulls out of her and sits in the love seat. Rose was almost shocked at how empty she felt at this. Rosie offered her hand, and she takes it. She stands up, only to be redirected to sit in Dave's lap. She feels his dick come to rest between the cheeks of her small ass. Rose on a whim decides to rub back against the hard member. She hears him hiss inward at this and smiles to herself. She feels his hands grip her hips and he starts to grind her back against him. She moans at this. He was really strong, and feeling his strength like this was really doing it for her. Even more than the look of his muscles.  
"You going to spend the entire day dry humping, or are you going to get back to fucking me proper?" Rosie asks, leaning over the grinding pair and grabbing hold of Dave's hands. She leans in over her shoulder to kiss Dave as she leads his hands down her legs to rest under her thighs. She pulls back and gently pushes up, clearly instructing Dave to lift Rose up. And lift her he did. Rose felt him support her weight seemingly effortlessly as she is lifted off of his lap. She reaches back to put her hand on his arm to better keep balanced. She felt his bicep flexing as he positions her over his cock. Then he slowly lowers her back down. She feels herself being stretched out again. She had already begun to tighten up again from the brief time he had pulled out. But it was not long before he was once again bumping against the entrance to her cervix.

Rose enjoys the feeling of being filled up again. Then she sees Rosie leaning down between Dave's legs. She watches as she licks up the bottom of Dave's cock, from the base, straight to where it was connected to her pussy. She drags her tongue slowly over her clit, sending jolts of pleasure through her body, and causing her to clamp down even harder on Dave's intruding member. She cries out a bit at the sensation.  
Then Dave starts to move. Partially lifting her up and down, and partially thrusting his hips, he starts to fuck her. It's slow at first. Steady, shallow thrusts. But over time he starts pulling out more and more, and thrusting in just a bit more forcefully. He was very good. Not thrusting enough to hurt when he bottomed out. But hard enough that she could feel the power behind each movement. Before long, Rose felt like Dave was moving like a jackhammer. She cried out in ecstasy as her brother's dick flew in and out of her. Each inward thrust bringing his dick to kiss the entrance to her womb. She was having an increasingly difficult time keeping track of her surroundings. Too caught up in the vigorous fucking she was receiving. She feels Rosie's hands roaming her body. Groping her ass, rubbing her clit. But distinguishing between these various stimuli was becoming increasingly difficult. She felt the world melting away. Everything became white, as she felt her entire body seize up. Nothing mattered anymore, because she was in an ocean of bliss and ecstasy.

She couldn't tell how long she had lost touch with reality. A few seconds? A few minutes? It was legitimately hard to tell. When she came too, she heard voices, as her vision came back.  
"Sure she's alright?" Dave asks, his face swimming into view.  
"She's fine. She's just dealing with the best orgasm of her life." Rosie says.  
"Best orgasm so far you mean?"  
"Sure. Let's go with that?"  
"What's that supposed to mean?"  
She can still feel his dick inside her. But she was turned around so she was facing him. She isn't sure what compels her to do it, but she reaches up and grabs him by the back of the head, pulling him into a kiss. He seems shocked at first, but quickly recuperates, returning the kiss.  
"That was amazing Dave." She gasps as they break away from the kiss.  
"Glad to hear it. Hey is it OK if we keep going? I still kind of..." He says, letting the sentence drift off. She feels his dick twitching inside her.  
"Feel free, brother mine." She says. His reaction is predictable. His dick twitches strongly as his face takes on an expression she would expect on someone who just got punched in the gut. She feels him grip tightly onto her thighs before he starts thrusting again. Not quite the same speed or ferocity as before. She also feels something else. Rosie's hand is gripping the base of Dave's cock, which couldn't fit into her small cooch. She jacks him off while he fucks her. Before long, she could feel him twitching more violently. And judging by his expression, he was almost certainly coming soon. She can't help but want to tease him when he's like this.  
"Wow. Your dick is jumping around a lot in there. You must be close huh? Your sister's pussy feel that good?" She asks, enjoying the look of Dave's intense mixture of shame and arousal at her words. "You look so embarrassed by that. Me accusing you of liking your little sister's tight virgin pussy." Rose says, finding dirty talk come naturally here. She wasn't sure where this confidence was coming from. Maybe she was still riding high on her orgasm.  
"Don't worry about it Dave. Your sister doesn't mind if you're a pervert. Because she likes it. She likes that you're a pervert almost as much as she likes her big brothers thick, hard, cock."

That does it. Dave cries out, and thrusts as deep as he can inside her. Rosie jacks off the base of his dick as he cums deep inside. She feels the warmth of his cum as it pours into her deepest parts. She gets a warm fuzzy feeling from both the cum, and Dave's face as he cums. A few moments of bliss pass, as she feels him twitch in her depths, and slowly start to grow soft. She lifts herself off of him and rolls over onto the loveseat. As soon as she's off, her older self leans in and takes Dave's deflating dick into her mouth. She pulls off a moment later, his cock mostly clean.

"That was incredible." Rose says through heavy breaths.  
"Yeah." Dave agrees.  
"Watching myself get fucked was pretty damn hot. We need to do this more often." Rosie says.  
"I'd be down for that." Dave says.  
"So... I've been wondering. How long have you been... doing this? This relationship." Rose asks.  
"Heh. Sorry Rose. That's confidential." Rosie says.  
"Are you serious?"  
"Afraid so." She says.  
"So, now I'm supposed to know I end up fucking my brother in the future, but not know when? Am I supposed to get into other relationships and pretend I don't know this?"  
"Take it from me. You don't over think this time stuff. Go with the flow of things. Experience life. And don't focus on when something or other is going to happen." Dave says.  
"The something or other being me fucking my brother."  
"Yeah." Dave says.  
"Don't worry Rose. This thing with Dave is a long ways off. You have plenty of time to focus on other things and growing as a person. And when it happens, it happens." Rosie says.  
"More reassurance from someone who's already been in my shoes?"  
"Exactly. Sorry we have to fuck and run like this without giving more clues to your future. But that's just how things go." Rosie says.  
"You're leaving already?" Rose asks, disappointed.  
"Yeah. Sorry. We can't really stay." She says, gathering up her clothes while Dave does the same.  
"Well I suppose it can't be helped. Thanks for the experience though." Rose says.  
"You're welcome." Rosie says. Then Dave puts his arm around her, and they both fade away. Rose is left alone with her thoughts.

Eventually she gathers up her clothes, gets dressed, and makes her way back to the living quarters. She feels sore for a day or two afterwards, and has trouble looking Dave in the eye for more than a week. But eventually, she can act like nothing had ever happened in that far flung corner of the meteor. Until it was her turn to coerce Dave into bringing them back for some fun with her younger self.


End file.
